


The Babysitter

by TheOriginalSinner888



Series: Original Sins [3]
Category: Original Work
Genre: Cameras, Dirty Talk, Doggy Style, Eating, Exhibitionism, F/F, F/M, Face-Fucking, Face-Sitting, Groping, Lesbian Sex, Masturbation, Older Man/Younger Woman, Oral Sex, Scissoring, Sex Tapes, Sex Toys, Strap-Ons, Teasing, Underage Sex, Vaginal Fingering, Vaginal Sex, babysitter, sex on camera, sex with a minor, unprotected sex
Language: English
Status: Completed
Published: 2019-03-06
Updated: 2019-03-06
Packaged: 2019-11-12 17:58:32
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 5,338
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18015620
Author URL: https://archiveofourown.org/users/TheOriginalSinner888/pseuds/TheOriginalSinner888
Summary: Katie saw something she shouldn't have on her DILF of an employer, John.  And she sets on a mission to seduce him because of it.





	The Babysitter

“Stef, I need your help,” I told my best friend the second I saw her when we got to school. 

She seemed a little taken aback by my greeting but still asked, “Okay, with what?” 

I grimaced, “You can’t judge me.  Pinky promise!” 

She rolled her eyes and crossed her pinky with mine.  “Now, what do you need help with?” 

“Seducing my boss,” I cringed even as I said it.  But it had to be done. 

She gaped at me, “You want to fuck your boss?  You mean the  _dad_ you babysit for?  The  _married_ dad whose kid you watch?  Don’t you practically live with them too?” 

That was pretty much the situation.  A lot of the time they were at work so late that she was asleep by the time they got home.  She eventually started staying over in their guest room.  Even some of her belongings had migrated over so they could take her to school and she could get her work done. 

They were John, Mary and little baby Sam.  I started watching Sam after school last year, and sometimes over the weekends.  Mary wasn’t a very involved parent.  She was almost always working.  John seemed to be the one who wanted kids more, and was always there for his son.  It practically made my ovaries explode. 

“You can’t judge me!” I whined to her. 

“You said that before you decided me you wanted to bang your 36-year-old boss, Katie,” Stef pointed out.  “But I have to admit, he’s a total DILF.  But you’ve been with that family for like a year.  Why do you all of the sudden want to sleep with him?” 

I blushed, “Because I saw his cock.  Now I want it.” 

Her eyes bugged, “When did you see his cock?” 

I flashed back to that afternoon well over a month ago.  I had been cleaning up after little Sam, who had left a trail of toys from his room upstairs, all the way to the back patio.  Of course, this was after John got home early for once and Sam had promptly spilled his orange juice all over him.  John had had to go clean up.  “Watch him for a bit longer while I take care of this?” he had asked me. 

“Of course!”  

While he had gone upstairs, I had set Sammy in his high chair with a sippy cup of juice this time and set to cleaning up after locking the doors.  I had picked up his toys with the toy box in hand so I could end the trail in his bedroom before John got out of the shower.  I could hear the shower clearly in the hallway bathroom.  John always used that one since Mary monopolized all the space in the master bathroom.  What I hadn’t realized then was that he carelessly left the door wide open.  As I was crouching to pick up Sammy’s stuffed elephant, my attention was drawn into the room and my mouth had dropped when I saw him through the clear glass door of the shower.  I had never realized before how fit he was.  And as his eyes were averted and he was facing me, I saw his hands running soap over his cock and balls languidly.  He wasn’t hard obviously, but my mouth was still watering at the sight of him. 

I blushed as I told Stef all about this, “So?  Will you help?” 

She rose a questioning brow at me, “Help you with what?  I still don’t understand what you expect me to do.  It’s not like a lesbian like me could give you tips of getting a man’s attention.” 

“Okay, maybe I should just start from the beginning,” I sighed. 

“Maybe you should.” 

* * *

After seeing John’s cock, I knew I wanted it.  In my mouth.  In my cunt.  In my ass even if he was into that.  But how to go about that?  He had called me beautiful before.  I had even caught him looking at me sometimes.  It hadn’t bothered me before.  He had never made me uncomfortable and I thought it was only normal for him to look every once in a while.  Especially when summer hit us this month and I was dressing in shorts more and more often. 

But how was I supposed to move that up further.  Sometimes the family had me stay for dinner if they got home late but not too late to eat.  Half the time it was just John and Sammy.  So, I started by not wearing bras under my more see-through shirts, along with short shorts.  Sammy didn’t notice, of course, he was a baby.  But I could tell John noticed.  I could feel his eyes on my pink nipples under my white shirt when I focused on eating my food.  I wanted him to touch me.  I even saw him adjust his cock in his pants when he stood and thought I was paying attention to little Sammy. 

One day when he and Mary got home at the same time, I decided to shock him when he couldn’t respond at all.  Mary was handing me cash as per usual, extra for staying as late as I did, and said she’d drive me home tonight since she knew I had a test tomorrow.  As she went to greet Sammy before we left, I turned to John and gave him a teasing smile.  Wordlessly, I pulled my shirt up, exposing my perky little tits to his eyes.   

I saw his eyes widen comically as they zeroed in on my breasts and open his mouth to speak.  But all too soon I could hear Mary’s heels clicking on the tile and dropped my shirt just as she returned. 

A couple days later, I had ended up sleeping over, so Stef was picking me up for school since she lived nearby.  I was treated to breakfast with the little family.  Mary gave me some oatmeal while John prepared Sammy’s breakfast and sat down with the newspaper on the corner next to me.  It was then I knew that he liked my advances, and that my actions were working somewhat.  Because I felt his fingers started to skim the skin of my bare knee, slowly crawling up my thigh where my own hand was resting. 

Unfortunately, his touch was halted when I got a text that Stef was outside and I had to leave. 

I was back that night.  It was another late night for him and Mary.  I even went to bed before Mary got home.  I had helped John put Sammy to bed and went to change myself for bed.  I had decided just to wear a plain shirt and panties.  Not trying too hard, but definitely attracting attention.  I could hear John puttering about downstairs, locking the doors and windows, turning off the lights.  I prepared to open the door and ‘happen’ to walk out when he got up the stairs.  Just as I heard the floor creak on that spot at the top of the stairs, I walked out into the hallway, scantily clad. 

John cleared his throat when he saw me, “I can turn the heat down if you’re warm.” 

“No, no,” I said hastily.  “I’m fine.  This is how I usually sleep.” 

“Really?” he questioned, slowly approaching me.  “I’ve seen you when you’ve slept over before.  You wear pants usually.” 

“When I know you’re going to see me, yeah,” I muttered quietly, scared to make too much noise and scare him off. 

“And you didn’t think I’d see you now?” he asked me. 

“Possibly,” I whispered.  He was right in front of me now. 

“Well, I certainly am seeing a lot of you now,” he commented, his warm breath caressing my face. 

“You could do more than see me.” 

As if his self-control snapped, his hand was on my breast and was eagerly groping me, cupping the whole breast and squeezing harshly in pulsing movements.  I arched into him from against the wall. 

But when I reached for his cock in his fleece pants, he suddenly ripped himself away from me and muttered, “I--I can’t,” and ran into his room. 

I was obviously disappointed.  More importantly, I was horny as hell.  I huffed and marched into the guest room.  My laptop was still open on the desk in there, since I had been working on some homework before John got home.  An idea struck in my mind as I caught sight of the web cam.  Before I could lose my nerve, I dragged the desk over in front of the bed and situated my computer so the webcam was aimed at the middle of it.  I pulled up the video recording function and then slowly crawled onto the bed, making sure my head was cut off at the top. 

I had never done anything like this before.  But I was already soaking through my panties and had enough momentum not to chicken out as I started groping my own breasts the way he had just been doing.  I could see myself on the skin as I was recorded.  I wished I had packed my vibrator.  But I would have to make do with my fingers. 

I quickly stripped off my shirt, showing the camera my bare tits.  I bounced them a bit in my hands for his sake when he saw this, and twirled my fingers around my nipples, making them hard as I made breathless noises I hoped the microphone picked up. 

I then stripped off my panties carefully, spreading the folds of my cunt between my spread knees with my fingers.  I started whispering his name like a prayer as I stroked my slippery clit, wishing the real him heard me down the hall and would run over to join me. 

“John, please fuck me,” I whimpered as I sank two fingers inside myself, tilting my hips down in small circles.  “I’m so fucking wet for you.” 

After a few minutes of this, I really just wanted something to hump.  A wicked idea came to mind and I reached behind me to grab once of the pillows and shove it between my legs so I was straddling it.  Making sure it looked sexy on camera, I started to grind down on the pillow, pressing my clit into the slight scratchy pillow case. 

I made sure he could see my rolling hips and perky tits as I moved back and forth on the pillow.  I wanted him to imagine me riding his cock.  I let out little moans as I could feel a wet patch forming on the pillow under my pussy.  A warm wave of pleasure was threatening to overwhelm me.  I started moving faster and faster, just wanting to cum.  I made sure to moan his name as I squirted all of the pillow as I came.  Once my breathing evened out, I pulled the pillow out from under me to show the camera the big wet spot on the case before I ended the recording. 

Before going to sleep, I downloaded the file onto an email addressed to his phone’s personal email from an email address of mine he didn’t already have in his contacts.  I made sure to tag it NSFW and put in the body;  _You may want to watch this with earphones on,_ before saving it in my drafts.  I would send it while getting ready in the morning. 

I could tell he had watched over the next couple of days.  Because I caught him looking at me with eyes darkened with lust, shamelessly eyeing my ass and tits under my clothes.  Unfortunately, he had yet to make a move, even when we found ourselves alone.  I would have to up the ante to truly shock him into succumbing to our desires. 

* * *

“Where do I come into this equation?” Stef asked when I finished.  “I mean, I don’t know what else you could do.  You flashed your tits, got him to touch them, and even sent him a video of you masturbating to him.  I think he gets the message that you want him.” 

“But I need to make him want me enough to take the plunge and--” 

“And plunge into you?” she cut in before I could finish, grinning at her pun. 

“More or less,” I blushed.  “And I figured if exposing myself wouldn’t work, there was one more thing I could do.  Something that would make him a bit jealous and drive him crazy the way all straight men are driven crazy by the same thing.” 

She looked confused for a minute but when it dawned on her she immediately shrieked, “NO!  I don’t want him to know I had anything to do with this!  Or have a sex tape floating around out there.” 

“Please!” I begged her.  “We’ll show no faces, except maybe mine at the end.  Just compile a few shots and angles to make a good series of clips.  He’ll never know it was you.” 

“Why me?” she asked.  “Why not some slutty teenager that could get something out of it too?”

“Because you’re my best friend and I don’t trust anybody else with this,” I told her.  “And I don’t want to risk doing it with a guy and totally turning him off.”  She didn’t seem convinced so I really had to sprinkle it on.  “Please, Stef!  I will help you with calculus, and, and run lines with you for you audition, and cover for you and your next girlfriend with your parents, and I’ll make you cum!  Please, Stef!  I'd owe you big time!” 

I could tell she was slowly waning.  She sighed and quickly said, “All right fine.  But I will get you to make me cum, not on camera.  The video will focus on you only, not my pleasure.” 

“Deal,” I said, squealing and hugging her tightly.  I really did have the best friend in the world. 

* * *

My parents were out of town for the weekend and John had that weekend off so I didn’t need to watch Sam.  I invited Stef to sleep over Saturday so we could use daylight to make our little film.  I let her take the reins on what we would do, only interjecting to set up the web cam. 

We were hungry when we got back to my house from the mall, getting nice outfits for the video.  So, I made pizza for us to eat and asked her how she wanted to do this. 

“First, you need to get used to even being sexually involved with a girl, off camera,” she said sternly.  “I am not going through a million retakes because you’re nervous to be naked in front of me and touch me.” 

“Okay,” I nodded, eager to get this done.  After eating, we went upstairs to my room and before I could even open my laptop, she had thrown me to the bed and gotten on top of me, crashing her lips to mine.  So, this is what she meant?  All right then. 

I eagerly kissed her back like we were making the porno now and cupped her face.  She took my hands and led them to her breasts, groping mine in return.  It wasn’t unpleasant.  I knew I wasn’t a lesbian at any means, but doing this with my best friend felt nice. 

She cupped me through my shorts next and stroked me quickly.  We set to stripping each other until we were naked, just looking at each other. 

“Touch me.  Get yourself used to it.” 

She was laying across from me, both of us on our sides.  I started by cupping her breasts and running my hands over her nipples until they puckered up.  I stroked down her side and stomach until I was groping her ass.  She titled her leg up into a V so her pussy was exposed to me.   

“There too.” 

I shyly did so, running my fingers over her soft folds until they began to dampen.  Her hand was on my pussy all of the sudden, stroking me to a quick wetness. 

“You ready?” she asked. 

I nodded eagerly, wanting this as much as I wanted John now. 

We decided to do it on my plush carpet next to my bed so the computer could remain steady on the floor.  She laid down flat as I grabbed the laptop.  “First, we’re gonna show him me eating you out.” 

We situated the laptop facing her face since I would be straddling it and blocking her features.  He would probably get a peek at her breasts and chin, but mostly he would see my pussy and ass with her tongue on it. 

I pressed record before climbing on her, checking the camera angle was good before whispering for her to go.  I let out a harsh breath when her tongue swiped up my folds.  Part of me hadn’t really expected to enjoy this with her.  But I was.  I was practically dripping onto her face as she circled her tongue around my clit. 

Just as I was about to cum, she stopped.  She stopped the recording before her face showed and said, “Next -- scissoring.  It doesn’t really do much for us but guys love seeing it.” 

She guided me on top of her hips, straddling on of her thighs while she lifted her other leg over one of mine so our pussies were sliding against each other.  We set up the camera by her head so it only saw us from our tits down to our grinding cunts.  I was still sopping wet and that lubed us all up.  Once she hit record, I started frantically rubbing my cunt against her, our throbbing clits sliding against each other over and over again, letting out little moans with each little strike of pleasure. 

I could tell what she meant by this not doing much for us.  It felt good, it was stimulating.  But it wouldn’t make us cum.  It really was more for John’s benefit. 

Soon, she had us stop and said now it was time to make me cum and really drive John crazy.  Now, I was on my back and she was off digging into her backpack.  My eyes widened when I saw her come back with a strap-on on her hips. 

She smirked at me, “Let’s show him what it really looks like to fuck you.” 

She knelt in front of me and moved the camera so it caught my cunt and her hips and the strap-on.  She spread my legs and folded my knees up to my chest so my pussy was spread and on display for the camera. 

She aimed the tip of the modestly sized dildo at my folds and slid it up and down, gathering wetness on the toy once she pressed record.  “Moan for me.  Moan for John.” 

It was out of my control, the mewling noises coming out of my mouth.  When I wanted to moan Stef’s name, I moaned John’s instead.  The next minute, she was sliding it inside my cunt until her mound hit mine. 

“Oh fuck!” I whimpered at the feeling of something filling me.  I titled my hips into hers as she thrusted into me. 

She grabbed the leg farthest from the camera and draped my calf over her shoulder, grabbing my thigh and fucking into me harder. 

“Look at that cunt,” she grunted, winking at me.  That was for John. 

She had steadily began fucking me faster and faster until I was wailing in pleasure and squeezing around the dildo, my juices spraying out onto the toy as well as Stef, screaming my head off.  Once I started cumming down, still panting, I noticed Stef panning the computer around so it panned over my naked and quivering body until it focused on my pleasured expression.  Once I was completely calm, I ended the recording and closed the lap top. 

Stef gave me a look as she stood and took off the strap-on.  “Bed.  Now.  It’s my turn to cum.” 

I instantly got off the floor and laid out on the bed, wondering how I would do this.  She made the choice for me when she straddled my head and told me to lick her.  As soon as my tongue swept over her folds, I tasted the tangy wetness she was practically swimming in.  further on, she started humping my face, moaning out for me.

Not trusting my tongue to do the job alone, I started sliding finger after finger into her cunt until I had three fingers thrusting into her.  After that, it didn’t take long for her to cum. 

As she came down, laying limp next to me, she chuckled and said, “We may have to do that again.” 

“Maybe,” I agreed. 

* * *

I had quickly cut the clips together on windows movie maker and sent it to John from the previous email address.  In the subject I typed;  _This could be you._  

I only sent it to him on Thursday because I knew Mary was going out of town for a big conference that afternoon and I would be babysitting that night and Friday night.  Friday morning, I had a big test so I didn’t stay over.  But I knew John would watch the video after getting back home once he dropped me off.  I played with my pussy all Thursday night, gasping for Friday. 

After school on Friday, Stef cornered me and dragged me into a rarely used classroom.  She pushed her hand onto the front of my shorts and stroked me harshly until I was gasping and moaning and drenching her hand.  I didn’t get close to cumming before she pulled her hand out and licked her fingers with a smirk on her lips.  “Now you’re ready for John.” 

She gracefully drove me to daycare to pick up Sammy and then to their house and waited until we were inside to drive off.  I distracted myself from my horniness by playing with Sammy and feeding him.  It was almost eleven by the time John got home. 

“How was work?” I asked him as he walked in.  “I already put Sammy down, but I’m sure he’d love a goodnight kiss, even if he’s asleep.” 

He said nothing, eyeing me as he put his briefcase down, stripped off his jacket, and started undoing his tie. 

I gulped, hoping he wasn’t silent because he finally had enough with me.  I turned to the counter and unwrapped the foil from the meatloaf I had made for me and Sammy.  “Are you hungry?  There’s plenty left.” 

He was suddenly pressed into my back and aggressively shoving his hands into the front of my shorts, cupping my pussy through my soaked panties.  I slid my hand over his to encourage him.  “I’m not hungry for food.” 

I whimpered as his fingers pressed into my clit.  “Please, John!” 

His lips pressed into the shell of my ear as he hissed, “Go into my room, strip down and get your cunt ready for me.  You’re already pretty wet.  Wait for me there.” 

He ripped his hand out of my shorts and smacked me on my ass.  I squeaked and quickly ran off, not even looking at him for fear he would change his mind if he saw my raging blush.  I ripped into his room and stripped off my clothes except for my high socks, crawling onto the bed and lying on my back.  I pulled my legs up and started stroking my pussy lips, keeping me wet and wanting until he came to slide his massive cock into me. 

I could hear him going through his routine, locking up, turning off the lights.  He walked passed the open door without even looking in for me.  But once I heard him over the baby monitor giving Sammy a goodnight kiss, I understood.  When he appeared in the doorway, half his shirt buttons undone, I started stroking myself faster.  “Please John,” I gasped as he approached. 

He slowly walked to the end of the bed before he was standing there, between my spread legs, watching me touch myself.  He started undoing the rest of his shirt until it was completely undone. 

I watched, gushing around my fingers, as he stripped off his clothes.  Seeing him now was vastly different from when I saw him in the shower.  He was still fit, full of lean muscles.  But now his cock was rock hard and flopping against his thigh, as if searching for something wet and tight to fuck.  And I was perfectly willing. 

“Let’s see if you’re ready,” he hummed, slapping my hand away from my cunt and replacing it with his fingers digging inside me to see if I was wet. 

I moaned loudly, thankful he had shut the door on his way in, at the feel of his thick, calloused fingers in my pussy.  I was already cloaking every crevice of his knuckles with my juices. 

He groaned under his breath, “So fucking wet.  But you gotta get me wet too.”  

I wasn’t sure what he meant as he yanked his fingers out of me, making me whimper in disappointment.  He fisted his cock and winked at me. 

“Take me in your mouth,” he ordered.  “Get me ready to fuck that pussy.” 

I eagerly flipped onto my knees and crawled towards him.  He grabbed my head by my hair and guided my mouth onto him.  He was too long for me to swallow all of him, but he seemed satisfied with what I could take. 

I rocked back and forth so my mouth bobbed over him, making sure to coat him heavily with my saliva.  I moaned around his cock when I felt his fingers reached behind me and start stroking my folds. 

“You’re so fucking wet and warm,” he groaned above me.  “I’m gonna fuck you all night long.” 

I could not fucking wait. 

When he was satisfied with my, ‘small fucking mouth’ he yanked me away and tossed me onto the bed.  “Same position as that fucking cocktease of a video you sent me.” 

Smirking, I pulled my legs up like Stef had done.  His tip was instantly sliding against my folds and then thrusting into me to the hilt.  I groaned a bit uncomfortably at first.  He was bigger than anything I’d ever taken before, and it was definitely stretching me to my limits. 

He guided my hand to my clit and said, “Just rub yourself and relax.  You’ll adjust.” 

I started pressing into my clit in wide circles with my fingers as he moved his cock in and out of me. 

I could hear squishing sounds every time he pushed into me and watched his eyes clench shut in pleasure.  I couldn’t believe this was finally happening.  It was better than anything I could have fantasized in my head while touching myself.  I feared I would be ruined for my vibrator by the time he was done with me. 

He grunted as he plunged into me, standing on his knees and pulling my hips up to meet him with a series of slapping sounds as our skin collided.  In the quickest turnaround ever, I could feel an orgasm begin to wash over me. 

“Oh, fuck, John!” I whined, tossing my head back as my walls collapsed on his dick moving inside me. 

He groaned at the feeling and grinding into me for a bit before he sat back down on his haunches.  Without dislodging his cock from my pulsing pussy, he grabbed my upper body and pulled me up so I was straddling his legs.  He planted my feet on the bed and guided me up and down to ride him. 

“Make sure to scream my name every time you cum,” he growled before planting his lips on mine as I bounced on his cock.  It hit every sensitive part of me. 

Before long, I was cumming again.  I even squirted!  The juices just sprayed out of me, drenching his cock and thighs with my cum.  He groaned even louder, “I love a pussy that squirts!  Such a tight little cockslut, aren’t you?” 

I don’t know why, but that just turned me on more.  “Yes, yes, I'm your cockslut!” 

He roughly tossed me back onto the bed and flipped me over onto my stomach.  He pulled me up onto my knees with my ass in the air before he was pounding into me from behind at breakneck speeds.  Every now and then I could feel his head butting into my cervix with a small twinge of pain, but it wasn’t enough to overwhelm the absolutely staggering pleasure I was feeling. 

I rocked back and forth on his cock, begging for him to make me cum again.  I could feel his cock throbbing inside me and knew that on the next one, he might cum with me.  Oh, how I wanted to feel his hot cum filling me up. 

I heard him growl and then his arms were pulling my upper body up so my back was pressed against his chest.  One hand cupped my breast while the other wrapped around my throat as he fucked up into me.

“Oh, fuck, John, please, please!” I begged and pleaded, almost in tears of pleasure and his hard cock plundered my cunt. 

“I’m gonna blow my load inside you, slut,” he hissed.  “Taunting me with your body.  Your tits, and ass.  Sending me those videos.  I know you don’t want me to pull out.  You want me to empty out my balls into your womb, tainting you with my seed.” 

My pussy clenched around him, desperate for his words to come into effect.  “Yes, please, John!  give me all your cum!” 

His hand left my breast to flick my clit.  The hand around my throat tightened until I could do nothing but gasp for air while he fucked me.  He growled into my ear that he was gonna fill me up, but he wanted to feel my tight cunt squeeze his dick even more first. 

With a powerfully rough swipe on my clit, I was hurdled into the most powerful climax I had ever felt before.  Feeling my walls clutch around his cock, he let go of my throat and pushed my chest back into the bed as he grabbed my ass and pistoned into me. 

He let out a loud yell as he came.  I could feel lava hot liquid coating my insides, all the way inside me.  He pulled out mid-stream, pressing his head just inside my pussy as he finished painting my walls with his cum, gasping the whole time, just as I was panting.  As he pulled his head away, I could feel dripples of cum slide down my clit. 

He collapsed onto the bed next to me and I figured it was safe enough to fall limp myself, trying to catch my breath as I watched his chest rise up and down.  He looked at me through the sides of his eyes and I felt a sharp slap to my ass.  I whimpered a bit, wondering what his recover time was. 

“Who was in that second video with you?” 

“I promised her I wouldn’t tell you that,” I whispered hoarsely. 

He smirked, “Was it that best friend of yours that drops you here?” 

I sighed.  Stef’s cover was blow.  “At least I didn’t  _tell_ you.” 

He chuckled.  “You think you could talk her into joining us next time?” 

I gave him a look.  Wasn’t I enough?  “She’s a lesbian.”  I noticed his cock get half-hard at my words.  Did guys really get that turned on over some girl on girl action?  “But maybe I could convince her to help me put on a little live show for you.” 

“That’s my girl,” he growled, flipping me onto my back and crawling over me.  I felt his suddenly rock-hard cock plunder my sopping cum-filled pussy, and knew I was in for a long night. 


End file.
